


It's A Terrible Life

by glowydean



Category: Supernatural
Genre: Boss/Employee Relationship, Daddy Kink, Dirty Talk, M/M, Masturbation, PWP, Phone Sex, Sexting, Submissive!Dean, light dom/sub play, submissive/dean
Language: English
Status: Completed
Published: 2013-09-04
Updated: 2013-09-07
Packaged: 2017-12-25 14:50:54
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 3,937
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/954411
Author URL: https://archiveofourown.org/users/glowydean/pseuds/glowydean
Summary: <blockquote class="userstuff">
              <p>Dean's heart hammers wildly as he waits for his boss' response. That's when he realizes that he's sitting naked in a bathtub on a Friday night with a hard cock, practically sexting with his boss. And not just his boss, the CEO of the entire fucking company.</p>
            </blockquote>





	1. Overtime

He's not a workaholic.

No, not at all.

The fact that his blackberry is perched on the edge of the tub while he soaks his sore muscles only means that he is a dedicated employee and nothing more.

Soft classical music wafts through the speakers of the small radio perched on one of the corner shelves. He closes his eyes and hums contentedly. The water is warm and he could almost fall asleep here.

Key word, almost.

His mind is fixated on two things. Well, three things.

For one, he can't stop thinking about his new secretary; Castiel. He can't stop thinking about Cas' pretty blue eyes, or his tight, round ass, oh what he would give to see it minus the slacks; and the lips on that boy, Christ.

Dean chuckles and he lightly strokes himself under the water. He closes his eyes and imagines what it would feel like to have that pretty mouth around his cock, how it would feel if Castiel swallowed him down whole, how it would feel to fuck his throat. He lets out a soft moan as he strokes himself faster.

He feels that familiar pressure building and suddenly, just as he's getting ready to blow his load, his phone beeps.

"Fuck!" he curses out loud. He bites his bottom lip and lets go of his dick reluctantly. He feels the tendrils of his lost orgasm clawing at him, nipping at his heels. The feeling of loss settles on his chest and he quickly dries his hand on a towel and picks up his phone. "Who the fuck is this?" he mutters as he enters his password. His brows lift in surprise when he realizes that the message is from his new boss, Benjamin 'Benny' Lafitte.

Dean had met with Benny several times this week. He was attractive, he would give him that, and charming as fuck, with that southern drawl that made him want chicken and biscuits smothered in gravy with some sweet tea on the side. And that beard, oh, Dean had already imagined Benny rubbing that beard all over him, all over the soft flesh of his inner thighs.

Dean shivers and clicks on the message icon.

He smiles when he realizes that it's not some kind of mass text message, rather, it's just for him. Dean chuckles as he reads the message.

 **BL** : What's a guy gotta do to have some fun in this town, Smith? ;)

Dean bites his bottom lip and debates on what to say. Was Benny looking for fun fun? Or was he legitimately asking for some kind of night time activity?

 **DS** : What kind of fun did you have in mind, Mr. L?

He watches the screen, anxiously awaiting the little beep.

 **BL** : I don't want to say anything inappropriate to you, Dean.

 **BL** : You know what kind of fun I want.

Dean cocks an eyebrow and he feels a rush of excitement pool in the pit of his stomach. He feels his cock harden as he types out his message.

 **DS** : Nah, Mr. L. You have to be more specific.

 **BL** : Tell me, Dean, what are you doing right now?

Dean hums and his fingers fly across the keys.

 **DS** : Bath.

 **BL** : A big boy like you in the bath? Bubbles?

 **DS** : No bubbles. Just soaking in some hot water. Good for the muscles.

Dean's heart hammers wildly as he waits for his boss' response. That's when he realizes that he's sitting naked in a bathtub on a Friday night with a hard cock, practically sexting with his boss. And not just his boss, the CEO of the entire fucking company.

His phone remains silent for a few minutes and he panics. Perhaps Benny has decided that texting Dean wasn't a good idea? Maybe he thinks Dean will file some sort of sexual harassment claim?

"Fuck," he mutters angrily.

The phone beeps.

 **BL** : A picture would be nice. I'd love to see those muscles.

Dean's mouth dries up and he frowns. A photo? On the company phone? That was just asking for trouble.

 **DS** : Haha. You got me, Mr. L. I don't know if sending that on the company phone is such a good idea ;p

 **BL** : Dean. I'm the fucking CEO. Who gives a shit?

Dean blushes and chews on his bottom lip.

 **BL** : So? You gonna help a brother out?

Against his better judgment, he lifts himself up from the tub and quickly snaps several shots of his hard cock. He flips through them and chooses the best one, closes his eyes and sends it to Benny.

Almost immediately the phone dings.

 **BL** : Wow, brother. That's a nice muscle you've got there.

Dean blushes.

The phone dings again.

 **BL** : Mind if I call you?

The classical music is suddenly not loud enough and he puts the phone back down on the side of the tub.

He just sent a photo of his dick to his boss.

He just sent a photo of his dick to his boss, and now his boss wants to talk to him on the phone.

 **BL** : Dean?

 **DS** : Ummm. Mind if I ask why?

 **BL** : I want to hear your voice, Dean. And I want you to hear mine.

Dean pauses and then shrugs. What the hell, right?

 **DS** : Okay.

He stares at the word for a few moments and then hits the send button.

It takes Benny a few minutes to actually call, but when Dean answers, he blushes at the older man's thick drawl.

"Didn't think you were gonna pick up, sugar," he says.

Dean grins. "I was a little nervous, I won't lie," Dean admits.

"Oh, Dean. I just wanted to hear that sweet voice of yours. How's that cock? Still nice and hard?" Benny asks.

Dean swallows thickly. "Yeah," he rasps out.

"I want you to touch it for me, Dean. Wrap your fingers around that thick, pretty cock you have and give it a nice stroke, pretend it's me," Benny coaches.

Dean obeys and he strokes himself under the water.

"You good, Dean?"

"Yeah," Dean mumbles.

"Yes, what?"

Dean blushes. Was Benny asking him for what he thought he was asking him for?

"Uh…yes sir?" he asks.

Benny chuckles. "Good boy. Keep stroking it for me, Dean. So nice and thick. It must be heavy, huh? It must hurt, not having me there to do that for you. To take care of you."

"Yes, sir, so heavy," Dean chokes out.

"Don't forget your balls now. Give them a nice little squeeze," Benny says.

Dean does as he is told and a soft moan slips out of his throat.

"Feeling good, baby boy?" Benny asks.

"Yes, sir, so good," Dean says, his voice thick with need.

"Keep stroking that cock. Oh, Dean, if I was there I would stroke it for you. I would suck it and lick it and drink all of that come. You gonna come for me, Dean? Nice and pretty?" Benny asks.

"Uh huh," Dean breathes. His breathing becomes more ragged and he lets out another groan as he feels himself rapidly coming closer to the edge.

"You almost there, sugar?"

"Yes, sir," Dean gasps.

"Good. Fist that cock, Dean. Think about me suckin' on it. I'd milk that cock for you, Dean. Make you come so hard your whole body would shake. Then I'd fuck you Dean. You'd like that? Fuck you hard into your mattress. Make you cry out, you'd be walking with a limp for a while. I bet you'd like that? To get fucked in the ass. That pretty little cock of yours just bouncing against your stomach?"

"Yes, yes, oh God, Benny, I'm gonna come," Dean moans.

"Did you ask permission, Dean?" Benny says in a low voice.

Dean bites his bottom lip and cries out. "Please, Benny, please can I come?" Dean begs.

Benny chuckles and then whispers one word: "Come."

And just like that, Dean comes. "Fuck," he moans as come spurts out of his cock. He continues to jerk it, feeling his entire body spasm with the force of his orgasm. It sends waves of pleasure throughout his body. His toes curl up and he feels his stomach contract so tightly it almost cramps.

On the other end of the line, he can hear Benny chuckling.

"You alright, brother?" he asks.

Dean opens his mouth but no words come out. He licks his lips and continues to stroke his sensitive cock.

"I'm good," he says.

"Sounds like you had a good time," Benny says.

"Mmmhm, I sure did," Dean says with a grin.

"Maybe next time, I'll buy you dinner first," Benny says, and Dean can hear the smile in his voice.

He chuckles. "I get to pick the place?" Dean asks playfully.

"Anything you want, sugar," Benny drawls.

"Hey, Mr. L, does this count as overtime?" Dean asks.

Benny laughs. "Don't push your luck, pumpkin," he says.

Dean blushes.

"Good night, Dean," Benny says.

"Good night, sir," Dean whispers.

"Good boy," Benny says warmly before he hangs up.

Dean places the phone back down on the side of the tub and laughs.


	2. Whiskey, Neat

Dean sighs and angrily crosses out yet another line on the paper before him.

He's been working on this one proposal for what feels like forever, and nothing he comes up with sounds good enough. He tosses the paper down onto his desk and presses the heels of his palms into his eyes until he's seeing stars. He stays like this for a few beats, slowly pushing away his frustration, trying to clear his head. I have time, he thinks to himself. He gets up and stretches his arms over his head as far as they can go. He is interrupted, however, by a gentle knock at his door.

It swings open, hinges creaking and he is greeted by the sight of his new secretary, Castiel, his blue eyes flashing apologetically, followed by the C.E.O, Benny.

Dean clears his throat and plants his hands on his hips. It's been a week since him and Benny had their little…sexting fiasco, and he hasn't seen or heard from him since.

"Mr. Lafitte, sir," Castiel says.

"Thank you, Cas," he says stiffly.

"Mr. Novak, if anyone comes calling, we've stepped out," Benny drawls.

Castiel nods quickly. "Yes sir," he says.

"Good boy," Benny says. He watches Castiel with great interest as he awkwardly steps out of the room. Benny turns back to Dean and flashes a toothy grin at him. He sits down in the plush leather chair, left out for clients and crosses one leg over the other. "Aren't you gonna offer an old man a drink?" he asks with a smile.

Dean fights back a grin and his lip twitches. He walks over to his bar and hovers his hand over a bottle of whiskey.

"That's fine; neat," Benny orders.

Dean obediently pours out a drink for his boss and walks over to him. He hands him the delicate crystal glass and watches as he sniffs at the amber liquid before downing it all in one shot. Dean leans up against his desk and crosses his arms over his chest. The silence in the room is almost unbearable. Dean feels somewhat flustered and doesn't know what to say, while Benny just stares at him, somewhat predatorily, his blue eyes twinkling mischievously.

"That's a nice boy you've got there. You been with him yet?" Benny asks. He tilts his glass for another drink and Dean walks back over to the bar for the bottle.

As he pours Benny a drink, he chuckles nervously. "Yet?" Dean asks.

Benny looks up at him slyly. "Pretty boy like that. You can't tell me you haven't thought about it…dreamt about it maybe…bending him over and fucking his pretty little ass…" he says, looking down into his glass.

Dean flushes and shrugs nonchalantly. "So what if I have?" he asks boldly.

"Well, I'd invite him in but…we do need to keep up appearances," he says. He takes a measured sip of the whiskey. "Plus, I'd like to have you to myself first," he says with a devilish grin.

"So…are we gonna talk about what happened last week?" Dean asks hopefully.

Benny observes him from over the rim of his glass. "What do you want to talk about, sugar?" he asks while getting up. He walks up to Dean and leans in toward his ear. His breath is warm on Dean's skin. He smells like whiskey and aftershave and Dean shivers. "You want to talk about how hard I made you come, Dean?" he whispers in a dangerous voice. "About how you said, yes sir, like such a good little boy?" he growls.

Dean grips onto the edge of his desk as Benny presses closer to him, closing the space between them. "Or do you want to talk about how you begged me to let you come? Begged me, like the sweet, good, little boy you are?" Benny whispers.

Dean swallows thickly and looks up at Benny. He lets out a low moan when Benny casually brushes his hand against his cock.

"Oh, Dean, I want to fuck you right here, right now. I want you on this desk, legs spread wide, I want you to beg for it…" Benny says. He presses a soft kiss against Dean's neck, gently dragging his teeth across his skin. "Go lock the door," Benny orders as he steps away from Dean.

It takes Dean a few moments to recover and he just stands there, heart beating rapidly in his chest, watching Benny as he finishes his whiskey. Eventually, when he catches himself, he walks over to the door on shaky legs and turns the lock. When he turns around, Benny has already removed his suit jacket and he's looking at Dean expectantly.

Dean walks up to him and begins to remove Benny's cufflinks.

Benny watches him while he works, occasionally stopping him to drag him into a kiss, bruising his lips.

Dean unbuttons Benny's shirt and watches as he shrugs out of the crisp, white thing, letting out a soft gasp when he sees the tattoos on his arms and on his chest. He places a hand on Benny's chest, lightly tracing the strange and intricate tribal patterns.

Benny grabs Dean's hand and pulls it up to his mouth. He kisses Dean's knuckles and smiles at him. "What did I do to deserve a beautiful boy like you?" Benny asks.

Dean blushes and leans in for another kiss.

"Undress for me, sugar," Benny says.

Dean steps back and slowly begins to undress himself.

Benny grins at him and watches him as he takes his time to strip. "Leave the shirt on," Benny commands.

Dean's fingers freeze on the top button of his white shirt and he nods.

"C'mere," Benny breathes.

Dean allows himself to be pulled into Benny's warm embrace. He blushes when Benny squeezes down on his ass, kneading the tender flesh with his fingers.

"Gonna open you up nice and good," Benny whispers. He lets go of Dean and turns around to the desk. He moves some things around but leaves all of Dean's paperwork on top of the desk.

Dean smirks. "I need that report," he says.

"Fuck that report," Benny drawls.

Dean allows Benny to gently push him back onto the desk.

Benny gets down on his knees and he hooks Dean's legs over his shoulders. He leans in towards Dean's hole and he licks it tentatively.

Above him, Dean moans appreciatively at the contact, and Benny continues on with his ministrations. Benny takes his time and opens Dean's hole. He fucks him lightly with his tongue, with his fingers, and presses soft kisses on Dean's inner thighs. He bites down lightly on the soft flesh while he inserts finger after finger into Dean's hole, watching as they are greedily swallowed up by Dean's heat.

"You like that, sugar?" Benny asks.

Dean bites down on his bottom lip and nods. "Yes, sir," he moans out.

Benny has four fingers inside of Dean's hole and one by one, he removes them.

Dean whimpers at the gradual loss of being full. "Benny," he whines.

Benny chuckles. "I told you what I wanted earlier, didn't I?" he asks.

Dean moans. Benny wants him to beg. And Dean knows that Benny won't fuck him until he begs. "Please, Benny, please fuck me," he whispers.

Benny stands up and begins to unbuckle his belt. "What did you say, sugar?" he asks as he carefully folds his pants.

"Please, sir, please, I just…I need it," Dean moans.

Benny strokes his cock and grins. He presses the head of his cock against Dean's hole and watches as his body shivers in anticipation. He rubs the head of his cock up and down Dean's hole, teasing him, watching as he groans and writhes on his desk, stroking his own cock, praying for some type of release. Benny continues to tease him until he sees Dean's eyes shining with tears.

"Please, Benny, please, fuck me," he begs.

Benny wastes no more time and slides his cock into Dean's waiting hole.

Dean lets out a strangled groan and continues to stroke himself while Benny fucks him hard, pounding into him. They settle into a rhythm and Dean can't ever remember getting fucked so good. Benny presses soft kisses into his skin while he fucks him, tells him that he's beautiful and that he's a good boy, and it's all Dean has ever wanted. He lets out a sob as he continues to stroke himself, bringing himself closer and closer to the edge.

Benny watches him with a soft smile as Dean unravels beneath him. "That's it baby boy, come for me, come," he coos. He continues to fuck Dean and watch as he lies there, face flushed, mouth open, hand on his cock, as he thrust into his fist.

"Oh fuck, Benny, I'm gonna come," he moans.

Benny dips down for a kiss. "Come for me, Dean," he whispers.

Dean continues to jerk his cock and a few moments later, he comes with a strangled groan.

Benny catches his mouth with his own and kisses him, hard, while his cock spurts out threads of hot come onto his chest, all over his shirt. He can hear some of it flying off to the side and land with a thwack onto his paperwork but he doesn't even care. Benny continues his assault on his mouth, as he continues to pound into him.

Dean knows he's close when his thrusts become more wild and erratic and soon, Benny is coming, hard, inside of Dean, with a moan on his lips.

He pulls back and plants his hands on Dean's hips and thrusts into him, digging his fingertips into Dean's flesh so hard, he's sure he'll leave bruises. He rides out the wave of his orgasm with his cock nestled in Dean's ass, and he watches as some of it leaks out of Dean's hole and drips onto the floor.

The two of them regard each other silently for a moment and then Benny cracks a smile.

Dean puts his hand over his face and laughs. He can't get over this. How ridiculous this entire thing its. He's lying on his desk, come dripping out of his ass, his boss' dick still in his ass.

"You're so beautiful, Dean," Benny says as he leans over for another kiss.

Dean blushes.

Benny nuzzles him for a few moments, pressing soft kisses into his skin while he randomly thrusts into Dean's used up hole, laughing when Dean moans and wraps his hands around his large arms. "You like when I take care of you?" Benny asks.

Dean nods. "Uh huh," he mumbles.

"I want to clean you up. Will you let me?" Benny asks as he bites down on Dean's neck. He sucks on the flesh and nibbles on it.

"Yes," Dean says.

Benny gently slides his cock out of Dean's ass and shushes him when he whimpers.

"Third drawer," Dean says.

Benny walks behind the desk and opens the third drawer and finds a collection of lotions, colognes, and other items like baby wipes and a couple wash cloths. He takes the baby wipes and he kneels once more in front of Dean's hole and he presses another kiss against it before taking a wipe out from the packet. He takes his time and cleans Dean up, wipes down his cock and his hole until it's gleaming wet and smells soft and sweet.

Dean hums appreciatively as Benny cleans him up. He allows him to unbutton his come stained shirt and watches as he carefully wraps it up and puts it to the side.

Benny makes sure he catches every drop of come that had escaped from Dean's cock. When he's finally done, he's helping Dean get into a fresh dress shirt and watches him as he pulls on his gray slacks once more.

When Dean finishes, he rushes over to Benny and helps him get dressed. He buckles Benny's belt, his fingers fumbling for a second and he blushes when Benny chuckles.

"It's okay, sugar," he drawls.

After Benny is dressed, Dean helps him to put his cufflinks back on, something that he finds oddly comforting even though he doesn't know why.

"You had better get that secretary of yours to come in and clean up," Benny says as he observes the office.

"Yeah, maybe I will," Dean says smugly as he adjusts Benny's tie.

Benny flashes him with a predatory glance and Dean's hand freezes on his tie. "You are not to sleep with anyone else, you understand?" Benny growls.

Dean's lip twitches but he nods. "Yes sir," he says.

"There are some things we should probably discuss about this…relationship," Benny says. "That is…if you're interested in…"

Dean leans forward and cuts Benny off with a kiss. "Hell yes," he breathes.

Benny chuckles and hooks two fingers beneath Dean's chin. "I'll have my girl set something up for us, dinner, Friday," he says.

Dean nods.

"Be good, baby boy. I'll see you again soon," he says as he walks away from Dean and over to the door. Benny unlocks the door and winks at Dean before stepping out. He closes it softly behind him and Dean walks over to his bar and pours himself a drink. He looks around at the office. His desk is a mess, but everything else is fine. They had cleaned up the come on their own, but his paperwork was all creased up and some of it was still wet with come. He swallows his drink down, savoring the burn of it going down his throat. He shifts his weight on his feet, and he mulls over what just happened. His ass is deliciously sore and he knows that when he gets home, he'll find other souvenirs on his body when he inspects himself in the mirror.

He's distracted by a soft knock on his door. When he looks up, it's Cas, who enters with a shy, knowing smile on his face. "Mr. Lafitte said there were some things to clean up in here?" he asks.

Dean observes him for a moment, taking in his beautiful blue eyes, his dark hair and his lush lips. He nods his head toward his desk and pours himself another drink.

So, he couldn't sample the goods, yet, but what was stopping him from doing a bit of window shopping? He takes a sip of his drink, leans back, and enjoys the view.

**Notes for the Chapter:**

> so they finally did the thing in the office. next chapter might feature our favorite lil angel, cas uwu.

**Author's Note:**

> posted this initially on tumblr and decided to post it here as well. this series will probably be a bunch of random PWP drabbles set in the terrible life universe featuring dean smith, secretary!castiel and c.e.o!benny.


End file.
